Failure & Redemption

Strawberry89

Female
From
US
In college, I enjoyed being a party girl and having an active sexual lifestyle. I studied for my classes and on the weekends, I partied hard and shared my bed with many men and even some other women.

My senior year of college I met this man named Dustin and we hit it off as friends. We shared a lot of interest and just had a lot of fun together. Around three months after that our relationship turned sexual as well and we officially began dating.

After some time it looked like Dustin and I were in for the long hall so we began sharing an apartment and talking about the future. One thing that was important for both of us was an active sexual lifestyle. Neither of us wanted to tip toe around about being attracted to someone else or even maybe wanting to enjoy no strings attached sex with someone else. We decided to be sexually open and adventurous in that aspect.

Go forward almost a full year after that, Dustin, and I were still having a ton of fun with each other. Neither of us had taken advantage of our open sex policy. I was at my job when a man I had become good friends with approached me and confessed to be attracted to me. He also told me that if I ever wanted to take things further to just let him know. He was an attractive man and it sounded fun but at the same time part of me said to be good to Dustin. In the end, I flashed a smile but just said okay and walked off.

I went home and told Dustin about what had happened and how it had made me feel. Dustin then told me he had been attracted to one of his coworkers as well but something had been stopping him from going through with any advances. This was our crossroads moment. We both felt it was time to take advantage of the rule or let it go and be normal. That would not be a bad thing but it did not seem near as exciting, as if we were settling down.

Lucky for us a day later my college roommate called and invited us to a party that weekend. To be blunt my former roommate was a slut and great at finding parties focused in getting ******* and laid. We told her we would love to go to the party.

Party night came and I was so nervous it was ridiculous. I had still been going to parties but I had not been going to them with the intention of having sex with someone else while my boyfriend was there. I went with a cute outfit and off we went to the party.

Everything started like normal when we got to the party. We said hello to our friends, grabbed a few drinks, and started to talk with people. As I talked with people, I looked around at the men there considering whom I should approach and flirt with. I decided to battle my nervousness with more drinks and then some shots to back those up. The night was going great and everyone seemed to be having fun. I had even begun talking with a man that was funny and smelled good. The final nail in the coffin was when we decided to play in a beer pong tournament. I could tell as the tournament started that I was ******* already. The tournament did not go well for us as it seemed like we were chugging our beers at a fast pace. I was happy when the final glass was empty.

Dustin and I were talking but I could not remember the subject. I decided I needed to use the bathroom and then all of the sudden I was there. I did not remember coming into the bathroom but there I was. I stood up and pulled up my pants. In a flash, I was sitting next to Dustin watch people play beer pong. I did not remember actually leaving the bathroom. I know we had a goal but something was not right. I looked at Dustin and told him it was time for us to leave. I could tell he was going to ask me why but he looked at my face and just told me okay.

I did not remember saying goodbye to anyone as we left the party but Dustin told me we did. We drove for about two blocks before I asked him to pull down an alley and I proceeded to puke next to someone’s trashcans. The mission of starting our crazy sexual lifestyle had turned into me making terrible sounds and vomiting in an alley. Dustin took me home and got me into bed and I survived the ordeal.

The next day we spoke about it and decided maybe things needed to happen a bit more naturally. We chose to keep the rule open but not to rush things.

It was about two months later and Dustin was gone for a training seminar when my coworkers decided to go have drinks after work. I was glad to go with them. We went to this small bar and complained about work and other things. My driver for the evening was a man named Leon who was a tall ******* of handsomeness and not a drinker. We were friends, enjoyed talking to each other and had even flirted. He had come to our state following work and was working at our store part time for extra money. He did not have many friends and tended to be quiet. A few others and I had been working on breaking him out of that habit.

We finished dinner and Leon gave a couple of us a ride and dropped me off last. I asked Leon what his plans for the rest of the night were and he said to go home and watch TV. I told him it was better to do that with company and invited him in. We went into my apartment and turned the TV on as I got us some drinks. Water for both of us.

We finished one movie when Leon said he needed to make a phone call and stepped out onto our patio. It was at this moment it clicked that this might be the time. Leon and I liked each other and it felt natural. I had a few drinks but it did not feel like the alcohol was talking. I got up and went into the bedroom. I quickly stripped out of my clothes and opened my underwear drawer. I grabbed the first lingerie I saw which was a black thong and a red lace babydoll. I got them on and adjusted my hair slightly before heading into the hall.

Leon was still on the patio talking as I came to the entrance of the living room. I stood there so I could come out when he came into the living room but he could not see me from the patio. My heart began to race but at this point, I was in lingerie waiting to step out in front of a man that was not my boyfriend. I thought about what to say or do when Leon came back in. As I heard the sliding door open and close, all I managed to do was step into the living room and say I thought we could do something besides watch TV.

Leon said nothing, as he looked me over. It seemed like forever but he tossed his phone to the couch and approached me. He wrapped his arms around me and our lips met. I felt his tongue come out and I opened my mouth to him. We began to make out there in the living room. His hands traveled my body starting at my back and going down to my ass. Each of his hands squeezed a butt cheek pulling our bodies closer. When our lips finally broke apart all he said was wow and then he began kissing and sucking on my neck. One of his hands went from my butt to between my legs as he started rubbing me through my panties. I opened my legs to give him better access. This felt naughty and amazing to be doing.

I pushed Leon back and began undoing his pants. When the buttons were all open I dropped to my knees pulling down his pants and boxers at the same time. He had an amazing looking dick. His balls hung low and his semi hard cock hung with them. I took it in my hand and began stroking him. He was quickly getting hard in my hand. I was eager to wrap my mouth around him. He tasted great and I loved the natural smell coming off his body. I went down until I would almost gag and then came back up. I was not rushing but taking my time letting him feel the warmth of my mouth feel of my tongue. Leon made small noises as I did this. I was not sure when or if I wanted to stop. I thought about starting to fuck each time I pulled back but I thought maybe one more time and slid my mouth down him again.

Leon was the one to break us apart. He took his cock out of my mouth and told me to lay back. I lay there on the floor as this amazing black man undressed above me. Once naked he got on the floor next to me. His hands slid on the inside of my thighs and I opened them willingly. He found my now very wet pussy and started to rub it. His hands felt amazing. Leon then pulled my panties aside and his fingers found my entrance and pushed in. I let out an audible sigh as he did so. He slid them into me as far as they would go and then began working them back and forth. I started breathing heavier as he did so.

Leon’s free hand came up and pulled down the lace fabric covering my breast. He grabbed one of them and began sucking on my nipple. I could feel it actively hardening inside his mouth. As one nipple came out of his mouth, he grabbed the other breast and began sucking on that nipple. He went back and forth, as his finger started to bring me to an orgasm. I loved him handling me in this manner and the orgasm that came with it felt amazing. I will not lie I was also excited that I was finally making use of our naughty rule and looked forward to telling Dustin this later.

Leon paid attention to my body as the orgasm hit and my muscles tightened. He gave each nipple a last kiss and his fingers slowed down. As my body relaxed, he grabbed my panties on the side and pulled them down. I lifted my hips as my panties came off me. Leon then moved in between my legs and pushed them apart. He looked me in the eyes as we were in position before reaching down and guiding his hard dick inside of me. His fingers had felt amazing and now as that beautiful dick of his slid into me and opened, I up I let out a huge moan.

Leon went until our bodies were against each other and then he began to thrust back and forth. He started slow but then his pace quickened. As this happened I began to lose control. I could not control my breathing. I could not keep the sighs and moans coming from my mouth to a low volume, my breast shook with each thrust. I gave up and went along for the amazing ride as it felt like waves of pleasure were going through my body with each thrust. My second orgasm came quick and hard. All my muscles tried to tighten on Leon but it did not even slow him down. I felt like a rag doll or a fuck doll as Leon worked me.

I was actually getting close to another orgasm before Leon’s thrust started hitting hard and he was pushing on my body hard and breathing deep. Leon took a final hard thrust into me and let go of a huge moan of his own. It was at this point I felt warmth spreading through my body and I could actually feel his dick pulsing and shaking inside of me. We stayed in that connected position catching our breaths as Leon continued to let go inside of me. I was not sure the exact amount of cum he was shooting into me but I had a good idea of how much it felt like.

We finally had to separate and my body felt numb. Standing up seemed like it took all of my strength. We smiled and Leon grabbed his clothes and headed to the bathroom as I went to the bedroom. I turned on the light and looked at myself in the mirror. My hair was all over the place and my breast hung free. The little skirt part of the babydoll was up above my stomach. My pubic hair had semen and a mix of other juices I am sure in it. I took off the lingerie and grabbed some PJ pants and a tee.

I came back into the living room and Leon was dressed and smiled at me. We made some small talk and he said it was time to be going. I went with him to the door where we kissed again and then he left. I went inside, grabbed my phone, and thought how to tell Dustin. I decided he might appreciate some humor so I simply typed guess who just got fucked and hit send.
 
In college, I enjoyed being a party girl and having an active sexual lifestyle. I studied for my classes and on the weekends, I partied hard and shared my bed with many men and even some other women.

My senior year of college I met this man named Dustin and we hit it off as friends. We shared a lot of interest and just had a lot of fun together. Around three months after that our relationship turned sexual as well and we officially began dating.

After some time it looked like Dustin and I were in for the long hall so we began sharing an apartment and talking about the future. One thing that was important for both of us was an active sexual lifestyle. Neither of us wanted to tip toe around about being attracted to someone else or even maybe wanting to enjoy no strings attached sex with someone else. We decided to be sexually open and adventurous in that aspect.

Go forward almost a full year after that, Dustin, and I were still having a ton of fun with each other. Neither of us had taken advantage of our open sex policy. I was at my job when a man I had become good friends with approached me and confessed to be attracted to me. He also told me that if I ever wanted to take things further to just let him know. He was an attractive man and it sounded fun but at the same time part of me said to be good to Dustin. In the end, I flashed a smile but just said okay and walked off.

I went home and told Dustin about what had happened and how it had made me feel. Dustin then told me he had been attracted to one of his coworkers as well but something had been stopping him from going through with any advances. This was our crossroads moment. We both felt it was time to take advantage of the rule or let it go and be normal. That would not be a bad thing but it did not seem near as exciting, as if we were settling down.

Lucky for us a day later my college roommate called and invited us to a party that weekend. To be blunt my former roommate was a slut and great at finding parties focused in getting ******* and laid. We told her we would love to go to the party.

Party night came and I was so nervous it was ridiculous. I had still been going to parties but I had not been going to them with the intention of having sex with someone else while my boyfriend was there. I went with a cute outfit and off we went to the party.

Everything started like normal when we got to the party. We said hello to our friends, grabbed a few drinks, and started to talk with people. As I talked with people, I looked around at the men there considering whom I should approach and flirt with. I decided to battle my nervousness with more drinks and then some shots to back those up. The night was going great and everyone seemed to be having fun. I had even begun talking with a man that was funny and smelled good. The final nail in the coffin was when we decided to play in a beer pong tournament. I could tell as the tournament started that I was ******* already. The tournament did not go well for us as it seemed like we were chugging our beers at a fast pace. I was happy when the final glass was empty.

Dustin and I were talking but I could not remember the subject. I decided I needed to use the bathroom and then all of the sudden I was there. I did not remember coming into the bathroom but there I was. I stood up and pulled up my pants. In a flash, I was sitting next to Dustin watch people play beer pong. I did not remember actually leaving the bathroom. I know we had a goal but something was not right. I looked at Dustin and told him it was time for us to leave. I could tell he was going to ask me why but he looked at my face and just told me okay.

I did not remember saying goodbye to anyone as we left the party but Dustin told me we did. We drove for about two blocks before I asked him to pull down an alley and I proceeded to puke next to someone’s trashcans. The mission of starting our crazy sexual lifestyle had turned into me making terrible sounds and vomiting in an alley. Dustin took me home and got me into bed and I survived the ordeal.

The next day we spoke about it and decided maybe things needed to happen a bit more naturally. We chose to keep the rule open but not to rush things.

It was about two months later and Dustin was gone for a training seminar when my coworkers decided to go have drinks after work. I was glad to go with them. We went to this small bar and complained about work and other things. My driver for the evening was a man named Leon who was a tall ******* of handsomeness and not a drinker. We were friends, enjoyed talking to each other and had even flirted. He had come to our state following work and was working at our store part time for extra money. He did not have many friends and tended to be quiet. A few others and I had been working on breaking him out of that habit.

We finished dinner and Leon gave a couple of us a ride and dropped me off last. I asked Leon what his plans for the rest of the night were and he said to go home and watch TV. I told him it was better to do that with company and invited him in. We went into my apartment and turned the TV on as I got us some drinks. Water for both of us.

We finished one movie when Leon said he needed to make a phone call and stepped out onto our patio. It was at this moment it clicked that this might be the time. Leon and I liked each other and it felt natural. I had a few drinks but it did not feel like the alcohol was talking. I got up and went into the bedroom. I quickly stripped out of my clothes and opened my underwear drawer. I grabbed the first lingerie I saw which was a black thong and a red lace babydoll. I got them on and adjusted my hair slightly before heading into the hall.

Leon was still on the patio talking as I came to the entrance of the living room. I stood there so I could come out when he came into the living room but he could not see me from the patio. My heart began to race but at this point, I was in lingerie waiting to step out in front of a man that was not my boyfriend. I thought about what to say or do when Leon came back in. As I heard the sliding door open and close, all I managed to do was step into the living room and say I thought we could do something besides watch TV.

Leon said nothing, as he looked me over. It seemed like forever but he tossed his phone to the couch and approached me. He wrapped his arms around me and our lips met. I felt his tongue come out and I opened my mouth to him. We began to make out there in the living room. His hands traveled my body starting at my back and going down to my ass. Each of his hands squeezed a butt cheek pulling our bodies closer. When our lips finally broke apart all he said was wow and then he began kissing and sucking on my neck. One of his hands went from my butt to between my legs as he started rubbing me through my panties. I opened my legs to give him better access. This felt naughty and amazing to be doing.

I pushed Leon back and began undoing his pants. When the buttons were all open I dropped to my knees pulling down his pants and boxers at the same time. He had an amazing looking dick. His balls hung low and his semi hard cock hung with them. I took it in my hand and began stroking him. He was quickly getting hard in my hand. I was eager to wrap my mouth around him. He tasted great and I loved the natural smell coming off his body. I went down until I would almost gag and then came back up. I was not rushing but taking my time letting him feel the warmth of my mouth feel of my tongue. Leon made small noises as I did this. I was not sure when or if I wanted to stop. I thought about starting to fuck each time I pulled back but I thought maybe one more time and slid my mouth down him again.

Leon was the one to break us apart. He took his cock out of my mouth and told me to lay back. I lay there on the floor as this amazing black man undressed above me. Once naked he got on the floor next to me. His hands slid on the inside of my thighs and I opened them willingly. He found my now very wet pussy and started to rub it. His hands felt amazing. Leon then pulled my panties aside and his fingers found my entrance and pushed in. I let out an audible sigh as he did so. He slid them into me as far as they would go and then began working them back and forth. I started breathing heavier as he did so.

Leon’s free hand came up and pulled down the lace fabric covering my breast. He grabbed one of them and began sucking on my nipple. I could feel it actively hardening inside his mouth. As one nipple came out of his mouth, he grabbed the other breast and began sucking on that nipple. He went back and forth, as his finger started to bring me to an orgasm. I loved him handling me in this manner and the orgasm that came with it felt amazing. I will not lie I was also excited that I was finally making use of our naughty rule and looked forward to telling Dustin this later.

Leon paid attention to my body as the orgasm hit and my muscles tightened. He gave each nipple a last kiss and his fingers slowed down. As my body relaxed, he grabbed my panties on the side and pulled them down. I lifted my hips as my panties came off me. Leon then moved in between my legs and pushed them apart. He looked me in the eyes as we were in position before reaching down and guiding his hard dick inside of me. His fingers had felt amazing and now as that beautiful dick of his slid into me and opened, I up I let out a huge moan.

Leon went until our bodies were against each other and then he began to thrust back and forth. He started slow but then his pace quickened. As this happened I began to lose control. I could not control my breathing. I could not keep the sighs and moans coming from my mouth to a low volume, my breast shook with each thrust. I gave up and went along for the amazing ride as it felt like waves of pleasure were going through my body with each thrust. My second orgasm came quick and hard. All my muscles tried to tighten on Leon but it did not even slow him down. I felt like a rag doll or a fuck doll as Leon worked me.

I was actually getting close to another orgasm before Leon’s thrust started hitting hard and he was pushing on my body hard and breathing deep. Leon took a final hard thrust into me and let go of a huge moan of his own. It was at this point I felt warmth spreading through my body and I could actually feel his dick pulsing and shaking inside of me. We stayed in that connected position catching our breaths as Leon continued to let go inside of me. I was not sure the exact amount of cum he was shooting into me but I had a good idea of how much it felt like.

We finally had to separate and my body felt numb. Standing up seemed like it took all of my strength. We smiled and Leon grabbed his clothes and headed to the bathroom as I went to the bedroom. I turned on the light and looked at myself in the mirror. My hair was all over the place and my breast hung free. The little skirt part of the babydoll was up above my stomach. My pubic hair had semen and a mix of other juices I am sure in it. I took off the lingerie and grabbed some PJ pants and a tee.

I came back into the living room and Leon was dressed and smiled at me. We made some small talk and he said it was time to be going. I went with him to the door where we kissed again and then he left. I went inside, grabbed my phone, and thought how to tell Dustin. I decided he might appreciate some humor so I simply typed guess who just got fucked and hit send.
Loved your story!
 
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